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Valdecoxib [systematic name: 4-(5-methyl-3-phenylisoxazol-4-yl)benzenesulfonamide], C
16H
14N
2O
3S, a diaryl-substituted isoxazole, is a non-steroidal anti-inflammatory drug (NSAID) that is used for the treatment of rheumatoid arthritis, osteoarthritis and dysmenorrhea pain. The planar isoxazole ring is oriented at angles of 22.2 (1) and 54.3 (1)° with respect to the phenyl and benzenesulfonamide groups, respectively. N—H
O and C—H
O hydrogen bonds and N—H
π, C—H
π and π–π interactions stabilize the crystal packing.
Supporting information
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.055
- wR factor = 0.179
- Data-to-parameter ratio = 20.6
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293
PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
PLAT420_ALERT_2_C D-H Without Acceptor N15 - H15B ... ?
PLAT480_ALERT_4_C Long H...A H-Bond Reported H7 .. N2 .. 2.82 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H8 .. O1 .. 2.82 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H11 .. O13 .. 2.65 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H17 .. O14 .. 2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H18 .. O14 .. 2.84 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H18 .. O13 .. 2.61 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H19 .. CG2 .. 3.10 Ang.
PLAT731_ALERT_1_C Bond Calc 0.90(3), Rep 0.900(10) ...... 3.00 su-Rat
N15 -H15A 1.555 1.555
PLAT731_ALERT_1_C Bond Calc 0.90(3), Rep 0.900(10) ...... 3.00 su-Rat
N15 -H15B 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.90(3), Rep 0.900(10) ...... 3.00 su-Rat
N15 -H15A 1.555 1.555
PLAT735_ALERT_1_C D-H Calc 0.90(3), Rep 0.900(10) ...... 3.00 su-Rat
N15 -H15B 1.555 1.555
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
15 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
6 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
1 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
7 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
4-(5-Methyl-3-phenylisoxazol-4-yl)benzenesulfonamide
top
Crystal data top
C16H14N2O3S | F(000) = 1312 |
Mr = 314.35 | Dx = 1.412 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 25 reflections |
a = 12.872 (2) Å | θ = 8–15° |
b = 9.282 (3) Å | µ = 0.23 mm−1 |
c = 24.761 (7) Å | T = 293 K |
V = 2958.4 (14) Å3 | Rectangular block, colourless |
Z = 8 | 0.35 × 0.30 × 0.20 mm |
Data collection top
Enraf–Nonius CAD-4 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 30.0°, θmin = 1.6° |
Graphite monochromator | h = 0→18 |
Non–profiled ω/2θ scans | k = 0→13 |
4295 measured reflections | l = −34→0 |
4295 independent reflections | 3 standard reflections every 120 min |
2167 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.179 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0714P)2 + 1.6196P] where P = (Fo2 + 2Fc2)/3 |
4295 reflections | (Δ/σ)max = 0.002 |
208 parameters | Δρmax = 0.32 e Å−3 |
2 restraints | Δρmin = −0.35 e Å−3 |
Special details top
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F2, conventional
R-factors R are based on F, with F set to zero for
negative F2. The threshold expression of F2 >
σ(F2) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F2 are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O1 | 1.15965 (17) | 0.3866 (3) | 0.51380 (9) | 0.0494 (6) | |
N2 | 1.1623 (2) | 0.5202 (3) | 0.48722 (11) | 0.0483 (7) | |
C3 | 1.1025 (2) | 0.5060 (3) | 0.44440 (12) | 0.0380 (7) | |
C4 | 1.0586 (2) | 0.3633 (3) | 0.44195 (12) | 0.0376 (7) | |
C5 | 1.0969 (2) | 0.2970 (4) | 0.48605 (12) | 0.0420 (7) | |
C6 | 0.9901 (2) | 0.2968 (3) | 0.40085 (12) | 0.0379 (7) | |
C7 | 0.8985 (3) | 0.2296 (4) | 0.41593 (13) | 0.0482 (8) | |
H7 | 0.8791 | 0.2293 | 0.4521 | 0.058* | |
C8 | 0.8354 (3) | 0.1628 (4) | 0.37838 (14) | 0.0478 (8) | |
H8 | 0.7739 | 0.1187 | 0.3891 | 0.057* | |
C9 | 0.8649 (2) | 0.1624 (3) | 0.32468 (12) | 0.0354 (6) | |
C10 | 0.9558 (2) | 0.2295 (3) | 0.30860 (12) | 0.0417 (7) | |
H10 | 0.9749 | 0.2299 | 0.2724 | 0.050* | |
C11 | 1.0179 (2) | 0.2959 (3) | 0.34657 (12) | 0.0405 (7) | |
H11 | 1.0791 | 0.3406 | 0.3357 | 0.049* | |
S12 | 0.78698 (6) | 0.07136 (8) | 0.27683 (3) | 0.0396 (2) | |
O13 | 0.8479 (2) | −0.0422 (2) | 0.25403 (10) | 0.0543 (6) | |
O14 | 0.69142 (18) | 0.0354 (3) | 0.30245 (11) | 0.0643 (8) | |
N15 | 0.7617 (3) | 0.1799 (3) | 0.22818 (13) | 0.0525 (8) | |
C16 | 1.0897 (2) | 0.6331 (3) | 0.40898 (13) | 0.0406 (7) | |
C17 | 1.0030 (3) | 0.6489 (4) | 0.37623 (13) | 0.0451 (8) | |
H17 | 0.9531 | 0.5765 | 0.3749 | 0.054* | |
C18 | 0.9908 (3) | 0.7723 (4) | 0.34559 (15) | 0.0567 (9) | |
H18 | 0.9328 | 0.7823 | 0.3235 | 0.068* | |
C19 | 1.0638 (3) | 0.8802 (4) | 0.34752 (16) | 0.0618 (10) | |
H19 | 1.0550 | 0.9633 | 0.3270 | 0.074* | |
C20 | 1.1497 (3) | 0.8650 (4) | 0.37979 (17) | 0.0625 (10) | |
H20 | 1.1993 | 0.9378 | 0.3810 | 0.075* | |
C21 | 1.1630 (3) | 0.7427 (4) | 0.41026 (15) | 0.0530 (9) | |
H21 | 1.2216 | 0.7333 | 0.4320 | 0.064* | |
C22 | 1.0883 (3) | 0.1486 (4) | 0.50805 (15) | 0.0576 (9) | |
H22A | 1.0355 | 0.1461 | 0.5354 | 0.086* | |
H22B | 1.1537 | 0.1204 | 0.5235 | 0.086* | |
H22C | 1.0702 | 0.0833 | 0.4795 | 0.086* | |
H15A | 0.724 (3) | 0.256 (3) | 0.2393 (16) | 0.077 (14)* | |
H15B | 0.8188 (17) | 0.189 (4) | 0.2075 (13) | 0.069 (13)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0506 (13) | 0.0556 (14) | 0.0419 (12) | 0.0000 (12) | −0.0073 (11) | 0.0018 (11) |
N2 | 0.0451 (15) | 0.0507 (16) | 0.0492 (17) | −0.0031 (14) | −0.0059 (13) | −0.0052 (14) |
C3 | 0.0305 (14) | 0.0431 (17) | 0.0404 (16) | 0.0018 (14) | −0.0009 (13) | −0.0063 (14) |
C4 | 0.0340 (14) | 0.0397 (16) | 0.0391 (16) | −0.0001 (13) | 0.0021 (13) | −0.0034 (14) |
C5 | 0.0395 (16) | 0.0492 (19) | 0.0374 (17) | −0.0001 (15) | 0.0066 (14) | −0.0023 (14) |
C6 | 0.0378 (16) | 0.0369 (16) | 0.0390 (17) | −0.0001 (14) | 0.0022 (13) | −0.0039 (13) |
C7 | 0.0489 (18) | 0.059 (2) | 0.0361 (17) | −0.0121 (17) | 0.0102 (14) | −0.0093 (16) |
C8 | 0.0410 (17) | 0.053 (2) | 0.0490 (19) | −0.0121 (16) | 0.0113 (15) | −0.0060 (16) |
C9 | 0.0369 (15) | 0.0297 (14) | 0.0395 (16) | 0.0010 (13) | 0.0017 (13) | −0.0073 (12) |
C10 | 0.0460 (17) | 0.0424 (17) | 0.0367 (16) | −0.0061 (15) | 0.0063 (14) | −0.0033 (13) |
C11 | 0.0391 (16) | 0.0430 (17) | 0.0395 (17) | −0.0079 (14) | 0.0091 (14) | −0.0012 (14) |
S12 | 0.0427 (4) | 0.0331 (3) | 0.0432 (4) | −0.0016 (3) | 0.0008 (4) | −0.0073 (4) |
O13 | 0.0666 (16) | 0.0377 (12) | 0.0586 (14) | 0.0090 (12) | −0.0053 (13) | −0.0149 (11) |
O14 | 0.0515 (15) | 0.0792 (18) | 0.0623 (16) | −0.0238 (14) | 0.0103 (12) | −0.0156 (14) |
N15 | 0.065 (2) | 0.0439 (16) | 0.0488 (17) | 0.0063 (15) | −0.0108 (17) | 0.0006 (15) |
C16 | 0.0383 (16) | 0.0407 (16) | 0.0428 (17) | 0.0010 (14) | −0.0021 (14) | −0.0083 (14) |
C17 | 0.0432 (17) | 0.0440 (18) | 0.0480 (19) | 0.0015 (16) | −0.0047 (15) | −0.0050 (16) |
C18 | 0.056 (2) | 0.051 (2) | 0.062 (2) | 0.0091 (19) | −0.0146 (18) | 0.0006 (18) |
C19 | 0.076 (3) | 0.0422 (19) | 0.067 (2) | 0.009 (2) | −0.001 (2) | 0.0044 (18) |
C20 | 0.066 (2) | 0.042 (2) | 0.079 (3) | −0.009 (2) | −0.007 (2) | −0.001 (2) |
C21 | 0.0455 (19) | 0.050 (2) | 0.063 (2) | −0.0053 (18) | −0.0113 (17) | −0.0014 (18) |
C22 | 0.063 (2) | 0.055 (2) | 0.055 (2) | 0.0032 (19) | 0.0104 (18) | 0.0054 (18) |
Geometric parameters (Å, º) top
O1—C5 | 1.348 (4) | S12—O14 | 1.424 (2) |
O1—N2 | 1.404 (4) | S12—O13 | 1.430 (2) |
N2—C3 | 1.317 (4) | S12—N15 | 1.603 (3) |
C3—C4 | 1.441 (4) | N15—H15A | 0.90 (1) |
C3—C16 | 1.479 (5) | N15—H15B | 0.90 (1) |
C4—C5 | 1.347 (4) | C16—C21 | 1.387 (5) |
C4—C6 | 1.482 (4) | C16—C17 | 1.388 (4) |
C5—C22 | 1.486 (5) | C17—C18 | 1.383 (5) |
C6—C11 | 1.391 (4) | C17—H17 | 0.93 |
C6—C7 | 1.385 (4) | C18—C19 | 1.375 (5) |
C7—C8 | 1.382 (4) | C18—H18 | 0.93 |
C7—H7 | 0.93 | C19—C20 | 1.372 (5) |
C8—C9 | 1.383 (4) | C19—H19 | 0.93 |
C8—H8 | 0.93 | C20—C21 | 1.373 (5) |
C9—C10 | 1.384 (4) | C20—H20 | 0.93 |
C9—S12 | 1.768 (3) | C21—H21 | 0.93 |
C10—C11 | 1.379 (4) | C22—H22A | 0.96 |
C10—H10 | 0.93 | C22—H22B | 0.96 |
C11—H11 | 0.93 | C22—H22C | 0.96 |
| | | |
C5—O1—N2 | 108.7 (2) | O13—S12—N15 | 106.10 (17) |
C3—N2—O1 | 106.0 (3) | O14—S12—C9 | 107.69 (15) |
N2—C3—C4 | 110.8 (3) | O13—S12—C9 | 107.80 (15) |
N2—C3—C16 | 117.5 (3) | N15—S12—C9 | 108.55 (15) |
C4—C3—C16 | 131.6 (3) | S12—N15—H15A | 112 (3) |
C5—C4—C3 | 104.0 (3) | S12—N15—H15B | 109 (2) |
C5—C4—C6 | 125.8 (3) | H15A—N15—H15B | 123 (4) |
C3—C4—C6 | 130.2 (3) | C21—C16—C17 | 118.9 (3) |
C4—C5—O1 | 110.5 (3) | C21—C16—C3 | 119.7 (3) |
C4—C5—C22 | 133.9 (3) | C17—C16—C3 | 121.3 (3) |
O1—C5—C22 | 115.5 (3) | C18—C17—C16 | 120.0 (3) |
C11—C6—C7 | 118.5 (3) | C18—C17—H17 | 120.0 |
C11—C6—C4 | 120.9 (3) | C16—C17—H17 | 120.0 |
C7—C6—C4 | 120.6 (3) | C17—C18—C19 | 120.5 (3) |
C8—C7—C6 | 121.4 (3) | C17—C18—H18 | 119.8 |
C8—C7—H7 | 119.3 | C19—C18—H18 | 119.8 |
C6—C7—H7 | 119.3 | C20—C19—C18 | 119.8 (4) |
C9—C8—C7 | 119.1 (3) | C20—C19—H19 | 120.1 |
C9—C8—H8 | 120.4 | C18—C19—H19 | 120.1 |
C7—C8—H8 | 120.4 | C19—C20—C21 | 120.4 (4) |
C8—C9—C10 | 120.5 (3) | C19—C20—H20 | 119.8 |
C8—C9—S12 | 119.3 (2) | C21—C20—H20 | 119.8 |
C10—C9—S12 | 120.1 (2) | C16—C21—C20 | 120.6 (3) |
C11—C10—C9 | 119.7 (3) | C16—C21—H21 | 119.7 |
C11—C10—H10 | 120.2 | C20—C21—H21 | 119.7 |
C9—C10—H10 | 120.2 | C5—C22—H22A | 109.5 |
C6—C11—C10 | 120.8 (3) | C5—C22—H22B | 109.5 |
C6—C11—H11 | 119.6 | H22A—C22—H22B | 109.5 |
C10—C11—H11 | 119.6 | C5—C22—H22C | 109.5 |
O14—S12—O13 | 118.51 (17) | H22A—C22—H22C | 109.5 |
O14—S12—N15 | 107.87 (18) | H22B—C22—H22C | 109.5 |
| | | |
C5—O1—N2—C3 | −0.7 (3) | S12—C9—C10—C11 | −177.7 (2) |
O1—N2—C3—C4 | 0.4 (3) | C7—C6—C11—C10 | 0.0 (5) |
O1—N2—C3—C16 | 179.1 (2) | C4—C6—C11—C10 | 177.7 (3) |
N2—C3—C4—C5 | 0.1 (3) | C9—C10—C11—C6 | −0.3 (5) |
C16—C3—C4—C5 | −178.4 (3) | C8—C9—S12—O14 | 11.5 (3) |
N2—C3—C4—C6 | −178.0 (3) | C10—C9—S12—O14 | −170.1 (3) |
C16—C3—C4—C6 | 3.6 (5) | C8—C9—S12—O13 | −117.4 (3) |
C3—C4—C5—O1 | −0.5 (3) | C10—C9—S12—O13 | 61.0 (3) |
C6—C4—C5—O1 | 177.7 (3) | C8—C9—S12—N15 | 128.1 (3) |
C3—C4—C5—C22 | −177.2 (3) | C10—C9—S12—N15 | −53.5 (3) |
C6—C4—C5—C22 | 1.0 (6) | N2—C3—C16—C21 | 21.1 (4) |
N2—O1—C5—C4 | 0.8 (3) | C4—C3—C16—C21 | −160.5 (3) |
N2—O1—C5—C22 | 178.1 (3) | N2—C3—C16—C17 | −155.6 (3) |
C5—C4—C6—C11 | −123.7 (4) | C4—C3—C16—C17 | 22.8 (5) |
C3—C4—C6—C11 | 54.0 (5) | C21—C16—C17—C18 | 0.0 (5) |
C5—C4—C6—C7 | 54.0 (5) | C3—C16—C17—C18 | 176.8 (3) |
C3—C4—C6—C7 | −128.3 (4) | C16—C17—C18—C19 | −0.4 (5) |
C11—C6—C7—C8 | −0.1 (5) | C17—C18—C19—C20 | 0.4 (6) |
C4—C6—C7—C8 | −177.8 (3) | C18—C19—C20—C21 | −0.2 (6) |
C6—C7—C8—C9 | 0.5 (5) | C17—C16—C21—C20 | 0.2 (5) |
C7—C8—C9—C10 | −0.8 (5) | C3—C16—C21—C20 | −176.6 (3) |
C7—C8—C9—S12 | 177.6 (3) | C19—C20—C21—C16 | −0.1 (6) |
C8—C9—C10—C11 | 0.7 (5) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N15—H15A···O13i | 0.90 (1) | 2.12 (3) | 3.010 (4) | 168 (2) |
N15—H15B···Cg3ii | 0.90 (1) | 2.59 (3) | 3.429 (4) | 156 (2) |
C7—H7···N2iii | 0.93 | 2.82 | 3.429 (5) | 124 |
C8—H8···O1iv | 0.93 | 2.82 | 3.529 (4) | 134 |
C11—H11···O13v | 0.93 | 2.65 | 3.383 (4) | 136 |
C17—H17···O14i | 0.93 | 2.61 | 3.273 (4) | 128 |
C18—H18···O14i | 0.93 | 2.84 | 3.387 (5) | 119 |
C18—H18···O13vi | 0.93 | 2.61 | 3.389 (5) | 142 |
C19—H19···Cg2vi | 0.93 | 3.10 | 3.708 (4) | 125 |
C21—H21···Cg1vii | 0.93 | 2.88 | 3.631 (4) | 138 |
C22—H22A···Cg3iii | 0.96 | 2.74 | 3.637 (4) | 157 |
Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) −x+2, y−1/2, −z+1/2; (iii) −x+2, −y+1, −z+1; (iv) x−1/2, −y+1/2, −z+1; (v) −x+2, y+1/2, −z+1/2; (vi) x, y+1, z; (vii) −x+5/2, y+1/2, z. |
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